Simon enrolled with the Department of Law in the University of Malaya, only to graduate from the newly set up Faculty of Law, University of Singapore in 1963.

Following his graduation, he spent a year as a Research Assistant in the Faculty where he discovered an interest in tutoring/mentoring law students.

He then spent 15 years in Human Resources, Marketing and General Management in MNCs such as Mobil Oil, Gulf Oil, Jardine Matheson and International Telephone and Telegraph (ITT), before returning to the law.

Simon commenced legal practice in Khattar Wong & Partners (KWP), where he was active in all areas of civil litigation, particularly in Building Contracts disputes, Insurance and Family Law. During his years with KWP, he mentored many pupils and, upon their call to the bar, guided them through their first trials. He also taught at the Practice Law Course conducted by the Academy of Law.

In 2003 he co-founded Legal Clinic LLC with Boon Theng, where he continues to be active in litigation. He recently led a successful appeal in the Court of Appeal on a landmark case involving damages in the Law of Torts.

Simon continues to enjoy mentoring the young lawyers and trainees in the firm.